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    A Novel Route to Enantioenriched α-Allyl α-Fluoroketones via Palladium Catalyzed Decarboxylation

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    Issue Date
    2008-08-21
    Author
    Barron, Briana R.
    Publisher
    University of Kansas
    Format
    42 pages
    Type
    Thesis
    Degree Level
    M.S.
    Discipline
    Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    This thesis details the development of a novel catalytic asymmetric route to α-fluorinated ketones. Enantioenriched α-fluoroketones were produced in good yields and high enantiomeric ratios via palladium-catalyzed decarboxylation of cyclic α-fluorinated β-keto allylic esters. A series of α-fluoroketones were produced to examine the scope and the conditions for this reaction. In contrast to previous routes toward α-fluorinated ketones, this route is advantageous for several reasons. First, this route avoids the issues associated with the regiospecific generation of fluorinated ketone enolates by forming the enolate in situ by palladium-catalyzed decarboxylation. Secondly, this method requires only a catalytic amount of non-racemic material in contrast to chiral fluorinating reagents which are required in stoichiometric amounts. Lastly, the β-keto ester substrates for this reaction are easily synthesized and readily fluorinated by electrophilic fluorinating reagents.
    URI
    http://hdl.handle.net/1808/4174
    Collections
    • Theses [3710]
    • Chemistry Dissertations and Theses [171]

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    785-864-8983
    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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